A reader recently posed the following question to me:
I’d like to ask your opinion on something — do rolled-up/cuffed pants make legs look longer, or shorter? I’m 5′ 7″ and started rolling up the bottom of my jeans/pants to look like a cuff, but was told it made my legs look shorter. (All the pants are pretty slim cut.) On the other hand, I’ve heard people say rolling up pants, sometimes even to the point where you can see skin/sock between pants and shoe, makes legs look longer.
I found this to be both an interesting and timely question. I’ve been seeing more rolled pants out on the street, some done well and others less so. When it looks good, this style can convey a classic and casual ease. Rolled khakis, paired with loafers, a washed oxford cloth button down, repp tie and blue blazer is about as Americana as you can get. Substitute cuffed khakis and the look is more dressed up but looses none of its inherent appeal.
Rolled jeans are a different story, principally because cuffing jeans is just wrong. I’ve never seen it and hope I never do. Jeans traditionally have a simple narrow hem and rolling them can create a nice casual effect. You can quite easily evoke a 1950’s James Dean vibe or a seaside clam digging feel.
When it come to the effect on height, in most cases rolled-up pants can have the same visual impact as cuffed pants. Cuffed pants have a more defined bottom than un-cuffed and therefore give the trousers a clearer visual start/stop line. On shorter men this can sometimes create the impression of shorter legs, especially with a wide leg or heavy break that leaves the pant leg puddling around one’s ankle.
The same can be said of rolled pants, especially when the pants are already too long. Once rolled up they look like little life preservers tied around the wearers’ feet. However, in both cases – cuffs or roll-ups – when the pants are trimmer and the length properly chosen, the look can be nicely neutral regardless of one’s height.
On taller men, the same problem of puddling can hold true, though the impact is less severe. It is also easier for tall men to accentuate their height by tailoring their pants with no break or even having them cut slightly too short. As my reader correctly points out the exposure of a little sock or ankle implies height via the leg being longer than the pants. This is a very tricky thing to pull off though, and can come across as an affectation
The same holds for rolled pants, but whether short or tall, make sure that the roll is only one or two folds deep at the most. Unless you are specifically trying to capture that walking-along-the-beach-at-the-Cape look, you want the roll to be neat and hold its shape. Personally, I try and avoid it looking too manicured and perfect; if I really want a cuff, I should go see a tailor.